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Hydrazine hydrate (1:1) → 5-(5-Amino-2H-pyrazol-3-yl)-3-[1-(2-chloro-phenyl)-ethoxy]-thiophene-2-carboxylic acid methyl ester

HRID 1171167
Notes
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Reaction equation

HRID 1171167 reaction equation
O.[NH2:2][NH2:3].[CH3:4][O:5][C:6]([C:8]1[S:9][C:10]([C:23](=O)[CH2:24][C:25]#[N:26])=[CH:11][C:12]=1[O:13][CH:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[Cl:22])[CH3:15])=[O:7]>CCO>[CH3:4][O:5][C:6]([C:8]1[S:9][C:10]([C:23]2[NH:2][N:3]=[C:25]([NH2:26])[CH:24]=2)=[CH:11][C:12]=1[O:13][CH:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[Cl:22])[CH3:15])=[O:7]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 667303243-[1-(2-Chlorophenyl)-ethoxy]-5-cyanoacetyl-thiophene-2-carboxylic acid methyl ester

Product 1

HCID 595539565-(5-Amino-2H-pyrazol-3-yl)-3-[1-(2-chloro-phenyl)-ethoxy]-thiophene-2-carboxylic acid methyl esterYield 29%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

Hydrazine hydrate (17.4 mg, 0.35 mmol, 1.1 Eq.) was added to a stirred solution of 3-[1-(2-Chlorophenyl)-ethoxy]-5-cyanoacetyl-thiophene-2-carboxylic acid methyl ester (115 mg, 0.32 mmol, 1.0 Eq.) in EtOH (4 mL) and the reaction heated at 80° C. overnight. The reaction mixture was concentrated in vacuo and purified by column chromatography (70/9/1 DCM/MeOH/Aq. NH3) to give the sub-title compound as a white solid (35 mg, 0.09 mmol, 29%);

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompurified by column chromatography (70/9/1 DCM/MeOH/Aq. NH3)

Sources & evidence

ORD record
ord-97e3ff3875364d5ab7fdf09b78574835
Source dataset
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07829590B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes